EP2874995A1 - Procede de preparation du diaminomaleonitrile - Google Patents
Procede de preparation du diaminomaleonitrileInfo
- Publication number
- EP2874995A1 EP2874995A1 EP13737315.5A EP13737315A EP2874995A1 EP 2874995 A1 EP2874995 A1 EP 2874995A1 EP 13737315 A EP13737315 A EP 13737315A EP 2874995 A1 EP2874995 A1 EP 2874995A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- process according
- catalyst
- ketone
- carried out
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
Definitions
- the present invention relates to a method of manufacturing diaminomaléonitril ⁇ .
- Diaminomaléonitriie (DA N) is known to be a precursor for the synthesis of nitrogenous rings such as imidazotes, pyrazines and purines. But recently the DAMN has proved to be a precursor for the synthesis of new lithium salts having interesting properties for improving the performance of Li-ion batteries (WO 2010/023413),
- Diaminomaléonitriie is conventionally obtained by polymerization of cyanhydric acid (HCN) using different types of catalysis.
- GB 1325620 describes the preparation of DAMN by tetramerization liquid phase HCN at a temperature between ⁇ ⁇ 40 ° C and below 0 ° C in the presence of a basic catalyst and at least one catalyst selected from-eo cyanogen and diiminosuccinonitrile.
- US Pat. No. 3,839,406 describes a process for the preparation of the DAMN comprising the following steps: (a) mixing at ambient temperature an alkaline catalyst chosen from sodium cyanide and potassium cyanide, in a solvent chosen from hexa-methyl-phosphoramide and hexa-ethylphosphoramide, (b) progressive addition of HCN and continued agitation of the reaction medium! for six hours with a molar ratio cyanide aleaisn / HCN less than 0.25, (c) dilution of the solution with hot water and (d) removal of a blackish amorphous polymer by flitration.
- an alkaline catalyst chosen from sodium cyanide and potassium cyanide
- the document CA 1000297 describes a process for the manufacture of diaminomalonitriy by polymerization of HCN in the presence of a compound chosen from oxides, hydroxides and cyanides of alkaline earth metals in a solvent chosen from n- methylpyrrolidone, dimethylsulfoxide and dimethylformamide.
- the starting reagent is hydrocyanic acid, which is a very toxic gas and whose use is highly regulated, which therefore limits access to the DAMN.
- the growing market for Li-ion batteries and interesting properties of the lithium salts synthesized from the DAMN will induce a high demand of DA N,
- the present invention relates to a process for producing diaminomalononitrile from a cyanohydrin ketone according to reaction 1.
- R and R ' identical or different, representing a linear or branched alkyl chain having from 1 to 5 carbon atoms.
- the process according to the present invention comprising at least one reaction step (1) can be carried out in the presence of a catalyst.
- the catalyst may be selected from the group consisting of inorganic or organic bases of which pK A is from 1 to 14, alkali or alkaline earth metal oxides and Lewis acids.
- Oxides that may be mentioned include potassium oxide, sodium oxide or calcium oxide. Silicon oxide may also be suitable.
- Lewis acids examples include trialkylaluminum, boron trialkyl or pentaalkylphosphorus.
- reaction can be carried out in the presence of an aprotic solvent.
- aprotic solvent mention may be made of nitriies, hexa-alkylphosphoramide, dimethylformamide, dimethylsulfoxide, toluene or oxyfene.
- the additives may also be present in the reaction medium.
- additives mention may in particular be made of mercaptans.
- the reaction temperature may be from -50 to 200 ° C, preferably from -20 to 150 ° C.
- reaction time can vary within wide limits. It is preferably between 1 and 96 hours, advantageously 1 and 72 hours. According to one embodiment of the process of the present invention, reaction 1 can be carried out in the presence of HCN according to the following scheme,
- the molar ratio of HCN / ketone cyanohydrin y / x may be between 0.001 and 2.5, preferably between 0.005 and 2.
- the molar ratio of the amount of catalyst to the total amount of reagents involved is preferably between 0.01 and 1,
- the method according to the present invention may further comprise at least one step of recovering the ketone formed as a co-product.
- the process may also include at least one catalyst recovery step.
- the process may also include a step of recovering excess cyanohydrin ketone.
- the process may comprise a step of purifying the diaminomaleonitile such as, for example, recrystallization or treatment with activated charcoal.
- the ketone cyanohydrin is acetone cyanohydrin.
- Example 1 illustrates the invention without limiting it.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1256893A FR2993560B1 (fr) | 2012-07-17 | 2012-07-17 | Procede de preparation du diaminomaleonitrile |
PCT/FR2013/051395 WO2014013151A1 (fr) | 2012-07-17 | 2013-06-14 | Procede de preparation du diaminomaleonitrile |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2874995A1 true EP2874995A1 (fr) | 2015-05-27 |
Family
ID=46963908
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP13737315.5A Withdrawn EP2874995A1 (fr) | 2012-07-17 | 2013-06-14 | Procede de preparation du diaminomaleonitrile |
Country Status (6)
Country | Link |
---|---|
US (1) | US20150197487A1 (fr) |
EP (1) | EP2874995A1 (fr) |
JP (1) | JP2015528803A (fr) |
CN (1) | CN104411680A (fr) |
FR (1) | FR2993560B1 (fr) |
WO (1) | WO2014013151A1 (fr) |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3629318A (en) * | 1970-03-18 | 1971-12-21 | Du Pont | Synthesis of diaminomaleonitrile from hydrogen cyanide as catalyzed by cyanogen or diiminosuccinonitrile |
JPS501250B2 (fr) | 1971-12-14 | 1975-01-16 | ||
US3806517A (en) * | 1972-02-25 | 1974-04-23 | Du Pont | Preparation of 4,5-dicyanoimidazoles |
US3897477A (en) | 1972-12-19 | 1975-07-29 | Kyowa Gas Chem Ind Co Ltd | Method of preparing diaminomaleonitrile |
JPS5623419B2 (fr) * | 1974-09-03 | 1981-05-30 | ||
GB1471851A (en) * | 1974-12-27 | 1977-04-27 | Sagami Chem Res | Diaminomaleonitrile derivatives and processes for preparing the same |
US4066683A (en) * | 1977-01-03 | 1978-01-03 | Nippon Chemicals Co., Ltd. | Process for the preparation of diaminomaleonitrile |
US20120036699A1 (en) | 2009-03-12 | 2012-02-16 | Safety Comploance Design & Services Pty Ltd. | Height safety system and method of installation |
-
2012
- 2012-07-17 FR FR1256893A patent/FR2993560B1/fr not_active Expired - Fee Related
-
2013
- 2013-06-14 JP JP2015522140A patent/JP2015528803A/ja active Pending
- 2013-06-14 WO PCT/FR2013/051395 patent/WO2014013151A1/fr active Application Filing
- 2013-06-14 EP EP13737315.5A patent/EP2874995A1/fr not_active Withdrawn
- 2013-06-14 US US14/415,003 patent/US20150197487A1/en not_active Abandoned
- 2013-06-14 CN CN201380036061.7A patent/CN104411680A/zh active Pending
Non-Patent Citations (1)
Title |
---|
See references of WO2014013151A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2015528803A (ja) | 2015-10-01 |
CN104411680A (zh) | 2015-03-11 |
US20150197487A1 (en) | 2015-07-16 |
FR2993560B1 (fr) | 2014-07-18 |
FR2993560A1 (fr) | 2014-01-24 |
WO2014013151A1 (fr) | 2014-01-23 |
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Legal Events
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RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: SCHMIDT, GREGORY |
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Effective date: 20160426 |